Valentina Boundless - Book 2

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The Prisoner’s Dilemma

The prisoner’s dilemma is a standard example of a game analyzed in game theory that shows why two completely “rational” individuals might not cooperate, even if it appears that it is in their best interests to do so.

The question is, who are the prisoners? Or is it just me that is the prisoner. As Nate mention to me the night after dinner at Tommy’s:

A gilded bird is still a caged bird.

So am I the bird and are my lovers’ battlefield my prison? And if this is the case, how do I get out of jail? I don’t have a Get Out of Jail Free card. If I am the prisoner of Tommy and Jake, then they both will stand for their truth and refuse to negotiate terms for early release.

And who are the two completely “rational” individuals? Last I checked there are four on the game board and none of us are “rational”. Well, maybe Nate. But is he rational when in actuality he refuses to take a chance?

So, I, the prisoner, what is my dilemma? That I have more than one man fighting for my love, and worse yet, that I may be in love with all three men. Who is capable of such a thing? How can I have my one true love when there are three that I love? Neither Snow White or Sleeping Beauty would ever be awakened from their sleep if there was no such thing as True Love’s first kiss. So which of the three men is my true love?

And worse yet, why is all of this taking up so much space on my mind. I need to focus on the deployment of our app and the work it will create for us. I don’t need or want these distractions.

Today I manage to work with my door shut and uninterrupted. Amazing how this feels. There is such comfort in programming. As endless and infinite as our possibilities are, it is a finite as our language needs to be. This is what I call structure. This is comfort. This is exactly what I need right now, to get lost in code. There is nothing sexy about writing code, but there is a powerful orgasm when what your code works.

Just as I spent my day in solitude, I am grateful for my solo barstool at Annie’s, satisfied with my dirty martini and Chrissie Hynde. Just as Brass In Pocket ended, I Love Rock-n-Roll cues up. It takes me a minute to realize that I didn’t pick that song this round, and another second to realize who did pick it.

“A scrawny, little bird told me you were looking for me.” His voice behind me sends chills up and down my spine. My Gods this man triggers my body in ways I have never known.

“Hey, stranger.” A bad attempt at being casual. I can feel him standing behind me and I am too scared to turn and see his face.

This entire time that Jake has been avoiding me has tortured me, but at the same time, I am relieved. The side of me that hates confrontation is partially okay with the fact that he is nowhere to be found. Now that he is here, I am so scared to face him.

As I have said before, I am Italian, we wear all our emotions on our sleeves for the world to see. The thing is, I am not sure which part of these emotions he will see. The part of me that misses him dearly? The part of me that enjoyed a pleasureful night with Tommy? The part of me that sits in ease and joy with Nate? Or the part of me that wants all of this to go away? If I turn around at this moment in time and see his face what will he read on mine?

“I didn’t think he would deliver the message,” I speak into my martini glass.

“Yeah, my brother is not that cool. He ran inside as fast as he could after you left, excited that you were looking for me.”

“And you? Are you excited that I am looking for you?” Still into my martini glass.

“Valentina,” Jake turns my stool so we are face to face.

Before he can even say another word his hands are on my cheeks, moving my face his, spreading my lips with his lips, exploring my mouth with his tongue. Just like that, we are back to that first night, our first kiss, our first exploration of one another. We can have a thousand more nights, and every kiss will always take me back to our first night.

“Jake,” I whisper breathlessly in his kiss.

“Oh get a room you two.” Teases our bartender.

I am sad but grateful for the interruption.

“Hey bro, I’ll take a McCallan, double, and on the rocks.”

“So, how was your week?” I suck at small talk.

“Tough, but I made it through. I am not going to lie, Valentina, I hate this.”

“I do too.”

“But it’s something you have to go through, my therapist says..”

I start to laugh, not meaning to hurt his feelings, which I undoubtedly did from the looks of him.

“I am so sorry, it’s not me laughing at you, it’s me laughing in joy. The fact that you are talking to your therapist about us. It’s amazing, so progressive of you.”

“I told you, I am working on myself and I don’t want to lose the man I am becoming any more than you want to remain a lost woman.”


“Sorry, didn’t mean that.”

“No, I deserve that.”

“I am trying to keep my cool in all of this but I am an extremely jealous man, that I can own. In the past, I did not handle big emotions well, my therapist helps me keep it all in check.”

“And is it all in check?”

“As long as I lock myself in my apartment and focus on work. Seeing you here, I am completely unglued.”


“Okay, stop apologizing. I know you didn’t ask for this, it sucks in every way for you too. And as I was saying, before you cruelly interrupted, my therapist, is suggesting that I head back to Paris and give you the space you need to figure out what is going on with you and Tommy.”

“I don’t want you to go.”

“I don’t either, but honestly, I can’t afford to let myself fall back into the dark place I lived for so long before.”

“I wish you would talk to me about that.”

“All the more reason to wait. You have enough on your plate, my dark past isn’t anything you need to add to your dilemma. Plus, I want you to know me as I am, and not judge me for my past.”

“I told you, I don’t judge.”

“Let’s not spend our last evening together talking like this.”

“Last evening?”

“Yes, I am leaving for Paris tonight.”

I can feel my heart shattering into a thousand pieces. If we weren’t surrounded by so many people, I would be in tears. Instead, I take a deep breath and try to shove the pain down deep. Doesn’t this pain mean that Jake is the one? But if he were the one, why was it so easy to sleep with Tommy? And how much fun did I have with Nate the other night?

“How is your launch coming along?”

“So far so good, I am nervous, but that is expected.”

“I am sure it will be a success.”

“What happens after the launch?”

“Well, I have been talking to Jessica about pitching a piece I want to write for the App. Once the readers get used to the App and it’s synchronized to the magazine, we will start to offer unique editorials to our App subscribers, a way of driving more traffic to our site.”

“That’s great. Do you know what you want to write about?”

“I figure I would start with something light and fun, not too heavy. Maybe different cooking schools in Europe, I can learn how to cook and enjoy new cities and cultures.”

“You cook?”

“Why does everyone seem so surprised by this?”

“Just another impressive part of you that is unexpected.”

“I am Italian, our lives revolve around great food and wine.”

“I give you that. The Irish side of me doesn’t cook, but the French side of me does love to eat.’

“Then let me cook for you.”

"My apartment in Paris has an impressive kitchen.”

“So let’s go. I will call in sick and fly to Paris with you tonight.”

“As much as I would love that, we both know that’s not the best for you at this time. The launch and all.”

“Yes, the launch and all.” And the heaviness that was starting to ease pushes down on my shoulders.

“So where do you want to start your cooking lessons?”



“I need to take claim of my ancestry. I am hoping my family can join. My parents haven’t been back to Italy since they were children.”

“That’s amazing. My therapist says you can’t move forward if you don’t settle your past.” I giggle again.

“Oh Gods, sorry, it’s just my friends back at Berkeley were secretly wishing I would see a therapist..”

“It’s a good time as any to start?”

“Yes.” I wanted to say it’s helped Nate a lot but that’s an entirely new can of worms that does not need to open.

“This sucks. I know you had a life before me, as I before you.”

“And I don’t want an after you.”

“Nor do I. But Tommy is here and you both have a lot to resolve. I don’t want to move forward with us if you have any doubts in your subconscious or worse conscious.”

“Maybe I should start seeing your therapist.”

“Maybe not mine, conflict of interest and all, but I will say, she helps me a lot. I will gladly ask her for a referral if you’d like.”

“Wouldn’t hurt.”

No way and egotistical Italian would see a therapist. My parents hashed out their issues the good old way, fighting and screaming and making up.

“There is a part of me that want’s to take you home and make mad, crazy love to you.”

“But the other part.”

“I know you have been with him. That, I know I can’t handle. The thought of you sleeping with us both at the same time.” The way it came out of his mouth, with such hurt, makes me want to run home and shower away my dirt.


“Please, don’t explain, it’s not something that words can work out.”

“So, is Joey behaving himself?”

“The best he can. He is heading upstate to hang out with the parents, my dad isn’t feeling great and he can’t afford to close down the bar, so ironically, Joey gets to play bartender for a few days. Funny, now he will learn what it’s like to deal with drunk assholes like himself.”

“I didn’t know your dad owns a bar.”

“The things you are deprived of when you refuse to get too personal with someone, you don’t get to know the specifics of their lives.”

“Touché! I deserved that one. It’s all just happening so fast. I mean the last time we were here at this bar, I didn’t expect to ever see you again. And now…”

“And now? What do you expect from me?”

“I don’t deserve what I expect from you.”

“Why don’t you tell me and let me be the judge of that.”

“Well, I have an idea to run by you about our current scenario, maybe you can see what your therapist thinks of it.”

“I am all ears.”

“I wish you were all hands.”

“Keep it PG-13.”

“Sorry, you are just so sexy and I just want so badly to have your hands all over me.”

“So you can add patience to the list of what you need to work on.”

“Okay, not sure if I like this serious side of you.”

“Yeah, it’s why I do my job so well, I have learned to be unaffected when necessary.”

“Again, not sure how I feel about that.”

“Let’s just get to your bright idea.”

“So, back to your discomfort about sex.”

“No, I am quite comfortable with sex, just prefer monogamy.”

“Okay, this jealous side of you is not fun.”

“My bad, I will refrain from commenting until I hear your pitch.”

“In truth, we never really got the chance to date. To get to know each other on an intimate level, not just on a physical level. Date me.”

“Gladly, but will you be dating just me.”

“I will be sorting out Tommy in the process, yes, but I genuinely want to be dating you.”

“Forgive me if this doesn’t sound as amazing as you may think.”

“Just think about it. I don’t want to lose you before even getting to know you. But at the same time, I do need to figure out what is happening between Tommy and me.”

“Then I will go to Paris as planned, and you figure out Tommy. Sorry, I can’t date you when you are dating anyone else. Maybe it’s selfish of me, although I don’t know too many men that would be okay with all of this.”

“That’s such a double standard, you can’t tell me you never dated more than one girl at a time.”

“That’s when I was younger and irresponsible. I told you, I know what I want with my life, I don’t want to play games.”

“Well, you are five years older than I am, so you can be a bit empathetic to my situation. All my friends my age, both men and women, are dating. It’s what we do in our 20s. I am just asking you to think about it.”

“I will think about it, in Paris.”

“I call bullshit! You have been going on and on for weeks about how hard you will fight for me. That was easy to claim when you didn’t have an opponent.” I knew this was hitting below the belt but Jake running away to Paris is a pussy move.

I am in no mood to argue. This is all too exhausting. Plus now I have to have the same conversation with Tommy. I should just go to Italy and forget all of them.

“Jake, it’s your life, do as you please.” I can turn off too.

“I am here. You know where to find me if you decide I am worth finishing the campaign you started!” Cold Gemini side in the house.

“Valentina, you know how I feel. When you know how you feel, you know where I will be.”

With that, he pays for our drinks, seals our deal with a kiss to blow my mind and wet my pussy, and leaves me on my bar stool. How can a man infuriate me, ignite me, and insensate me all at once? Jake just made it a lot easier for Tommy. He of all people knew I left Tommy because Tommy slowly took control of me and yet, Jake just robbed me of any predominance of him and me.

“Another please bartender.”

After a nice buzz hits me, I decide to pick up dinner and swing by Nate’s. It’s day two against the Red Sox so he will be home watching. He likes to be able to scream and yell at the TV without anyone around to shush him. Baseball made everything better yesterday, maybe it will again today.

I have a set of keys to his place as he has a set to mine. “Mi Casa, Su Casa!” He said when he handed me his keys my first day back in New York City. And so many times when I needed cuddles I could find my way there and crawl into bed safely with him. It was always nice to have someone to sleep with that has no expectations.

Now, all that may change, do I want that? What Nate and I have is so good, “don’t fix what ain’t broken” I always say. Now, Sylvia, has me thinking though, am I potentially missing a huge opportunity for my true soul mate? Nate does get me better than anyone.

I am sneaking into his apartment with beers and Nathan’s hot dogs, fitting for baseball. Suddenly I hear noises.

“Oh Nate baby, do that again please!”

I realize then, what an ass I am! Where do I get off thinking I am all that? With pleasure, he has a girlfriend, a hookup, or whatever she is. I am the only fool that never slept with him. I am the only idiot that didn’t capture the opportunity to call him mine. So set on the sacredness of finding myself.

I put the food and beers on the table and sneak back out. Allowing the tears to flow once I am safe in the taxi on my way home. Not sure again why I am crying. Just accepting that I can’t stop.

“When were you at my place?” Text from Nate.


“Was I alone?”



“No worries sounded fun.” Texting at least doesn’t let him know I am crying my eyes out.

“It was just sex. Sometimes I need more than my hands.” He has me laughing a bit like he always manages to do. “Did you still want to catch a drink? Watching the game on TV isn’t the same as those seats you got us the other night.”

“I should get to bed, I have a big day tomorrow. Now that the App has been in the hands of users, feedback will pour in, and we will need to incorporate that feedback into future versions of the app. Then I am hoping to meet with Jessica to pitch her my editorial piece.”

“Do you know what you want to write about?”

“Well, I think it’s time for me to claim the Italian in me, so I am thinking of getting to know my homeland via cooking schools. Kind of a Food for the Soul piece.”

“That’s amazing! You know they will accept your pitch. And when they do, can I hide in your suitcase?”

I want at that moment to beg him to come with me. But I couldn’t. This is a huge deal for my career and my self-love. Since I can remember I have wanted to take my family to Italy. Bringing any distraction along would not be the healing I need.

“Thanks. You always make me feel good.”

“Well let me know how it goes. I will be praying for you. Besos!”

“Good night sweetheart.”

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